During a(n illegal) poker night at Moe's, Homer and the others play with a retired Broadway star Laney Fontaine. After Homer loses to her while she's passed out, he brings her over to his house to meet his family, where she sees Lisa's innate talent at the saxophone and convinces her to forget about the $5,000 if she lets Homer and Marge take Lisa to New York to become a star. This causes Marge to become increasingly worried about Lisa's future, so they head out for New York (yet again) to get her.
- Barn Raising: Spoofed when Homer asks to use the bathroom and the Amish build him an outhouse.
- Bittersweet Ending: Lisa does prove to Laney that she has a bright future as a musician, but seeing her mother look concerned after leaving and Lisa having some doubts makes Laney fire Lisa to get both of them together.
- Continuity Nod: When Marge declares that the family must head to New York, Bart suggests making a house over there since they go there many times.
- Epic Fail: Homer losing to Laney at the poker game. She was drunk and passed out, and he believed he had the game until they saw her hand. Justified because it's a matter of luck to have the best hand.
- Lenny entering the room announcing himself, and then tripping and falling out the window. He's so focused on listening to his audio instructions the poker night is already over by the time he places a bet.
- Instant Expert: When Lisa throws her Saxophone at Bart in frustration, he catches it and immediately starts playing like he's practiced for years, commenting on how easy it is to do.
- It's more Fridge Brilliance when you remember that Homer and his children have all repeatedly shown incredible talent for music.
- Police are Useless: Moe tapes a sign over his bar's entrance door stating it's closed for an illegal poker night. Upon seeing the sign, Chief Wiggum tapes over the lower side of the sign.
- Screw the Rules, I Have Connections!: When the family tries to buy four tickets to see Laney's show, the ticketmaster says that the show's been sold out for some unknown reason. Homer pulls this trope off to get him inside.Homer: Uhh, say.. you're a union man, right? (Pulls out his Nuclear Power Plant Workers union card)
Ticketmaster: Well when you show me that, then I have no choice but to be corrupt. Enjoy your show.
- Shoo the Dog: Laney sees how unhappy Marge is about Lisa going on tour with her, so she fires Lisa so they can be reunited.
- Shout-Out: A scene inside Homer's head spoofs Inside Out, with Ned Flanders as Joy, Hans Moleman as Sadness, Milhouse as Fear, Comic Book Guy as Disgust and Groundskeeper Willie as Anger.
- Where the Hell Is Springfield?: Homer doesn't know which side of the Mississipi they're at and Lisa doesn't care.